Sesquiterpenes, detection

Semmler has detected a small qnaotitv of a sesquiterpene alcohol, and a phenol ether to which he assigned the name elemicin. This body h 3 a specific grariiy 1-063 at 30, refractive index 1 3365, aud boils at 144 to 147 - at lO mm. 

The chemical composition of C. sativa is very complex and about 500 compounds in this plant are known. A complete list can be found in [81] with some additional supplementations [2,82]. The complex mixture of about 120 mono- and sesquiterpenes is responsible for the characteristic smell of C. sativa. One of these terpenoic compounds, carophyllene oxide, is used as leading substance for hashish detection dogs to find C. sativa material [83]. It is a widespread error that dogs that are addicted to drugs are employed for drug detection. A9-THC is an odorless substance and cannot be sniffed by dogs. 

These two examples demonstrate clearly the usefulness of SPME to detect volatile compounds in complex mixtures. Among the few sesquiterpenes identified in the SPME extract for the two samples, longifolene can be considered as a biomarker of a substance originating from a conifer tree. The absence of abietane or pimarane diterpenoids is indicative of the use of parts of the tree with low resin content. 

The results obtained for these four samples highlighted the usefulness of SPME to get complementary information allowing a better characterisation of resinous substances. It is indeed possible to detect many non degraded mono- and sesquiterpenes in well preserved samples such as samples 1480 and 1485 and to detect some characteristic compounds in degraded samples such as sample 1484. 

Farnesylamine (123) (Fig. 20), a sesquiterpene alkaloid, was recently detected in whole extracts of Monomorium fieldi [129]. This compound had already be prepared by synthesis and found to display a whole range of biological activities. Among others, it inhibits arthropod molting, squalene synthesis, and the growth of malignant tumor cells, modulates human T cells and has anti-osteo-porosis activity [129]. 

Ferreira IF, Gonzalez JM. (2009) Analysis of underivatized artemisinin and related sesquiterpene lactones by high-performance liquid chromatography with ultraviolet detection. Phytochem Anal 20 91-97. 

Elsohly HN, Croom EM, Elsohly MA. (1987) Analysis of the antimalarial sesquiterpene artemisinin in Artemisia annua by high-perfomance liquid chromatography (HPLC) with postcolumm derivation and ultraviolet detection. Pharm Res 4 258-260. 

C) Inhibitory compounds can be identified in knapweed and these are probably released into the soil environment. However, sesquiterpene lactones were not detected in root exudates, where the major components were long-chain carboxylic acids. 

Fruit maturity has a major impact on peel oil composition. Terpenes are almost exclusively present in the oil from unripe fruit. As fruit mature, concentrations of aliphatic aldehydes and oxygen-containing terpenes and sesquiterpenes increase [30]. For example, nootkatone and a-selinenone were not detected in the peel oils from fully developed immature fruit, but the oil from ripe fruits contained up to 0.15% of these oxygenated sesquiterpenes. 

Volicifin has also been shown to activate a specific maize sesquiterpene cyclase gene, stcl, which is also activated in response to caterpillar feeding or regurgitant treatment (Shen et al., 2000). The transcription of stcl results in the production of a naphthalene-based sesquiterpenoid, which we have not yet detected from the many maize lines we have studied (e.g., Gouinguene etal., 2001). It would be interesting to see if this volicitin-induced substance shows attractiveness to natural enemies of the caterpillars that induce its production. 

Ginger oleoresin was extracted from rhizomes with ethanol, isopropanol or liquid carbon dioxide. All oleoresin samples had monoter-penes and sesquiterpenes. Carboxylic acids were found in organic solvent extracts for an extraction time of 2h. The components responsible for the pungent characteristic of the oleoresin gingerols were detected in... 

The yield and composition of the volatile fraction of the pentane extracts of leaves, stems and seeds of F. vulgare Mill, have been studied by Guillen and Manzanos (1996). The yield obtained from seeds was much higher than that obtained from leaves and stems. The volatile fraction of the pentane extract of the latter two has a higher concentration of terpene hydrocarbons and a smaller concentration of oxygenated terpene hydrocarbons than that of the seeds. Sesquiterpenes and the antioxidant vitamin E have been detected in the leaves and petroselinic acid in the seeds. Saturated aliphatic hydrocarbons with 25 or more carbon atoms have been found in all the plant parts. 

A methodological approach for an effective and reliable quality control of Chinese star anise [I. verum Hook. F.) was developed and validated by Lederer et al. (2006). A combined method of TLC and HPLC-MS/MS was used for differentiation ofvarious Ulicium species, especially Chinese and Japanese star anise. Species can be distinguished by their TLC flavonoid pattern. A sensitive and selective HPLC/ESI-MS/MS method was developed for the detection and quantification of lower admixtures of I. anisatum and of further toxic Ulicium species at a low concentration range using the sesquiterpene, lactone anisatin, as a marker. This assay includes a solid-phase extraction clean-up procedure with a high recovery (> 90%). 

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